Methyl iodide → HCID 86591646, compound

Participants

Reaction Conditions

Reaction Steps

A solution of trans-2-(5-Cyano-1-methyl-1H-indol-3-yl)-cyclopentanecarboxylic acid methoxy-methyl-amide (0.25 g, 0.84 mMol) in anhydrous tetrahydrofuran (15 mL) was treated with sodium hydride (0.067 g, 1.68 mMol). The mixture was stirred for 15 minutes and then treated with iodomethane (0.36 g, 2.52 mMol). After stirring 1.5 hours, the mixture was quenched with water and evaporated. The residue was dissolved in ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a hazy oil. This residue was dissolved in anhydrous tetrahydrofuran (5 mL), cooled to −45° C., and treated with lithium aluminum hydride (0.060 g, 1.57 mMol). The suspension was stirred for 1 hour and then quenched in the usual manner. The resulting mixture was filtered over sand and concentrated in vacuo. Silica gel flash column chromatography (50% hexanes, ethyl acetate) gave the product as a clear oil. 1H-NMR (400 MHz, CDCl3) δ 9.66 (1H, d, J=2.8 Hz), 7.94 (1H, m), 7.44 (1H, m), 7.42 (1H, m), 6.99 (1H, s), 3.76 (3H, s), 3.61 (1H, m), 2.98 (1H, m), 2.22 (1H, m), 2.02 (2H, m), 1.98 (1H, m), 1.87 (2H, m).

Provenance & Evidence